Synthesis, Superoxide Dismutase Mimetic and Anticancer Activities of Metal Complexes of 2,2-Dimethylpentanedioic Acid(2dmepdaH<mml:math id="E1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:math>) and 3,3-Dimethylpentanedioic acid(3dmepdaH<mml:math id="E2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:math>): X-Ray Crystal Structures of [Cu(3dmepda)(bipy)]<mml:math id="E3" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>2</mml:mn><mml:mo>⋅</mml:mo><mml:msub><mml:mrow><mml:mtext>6H</mml:mtext></mml:mrow><mml:mtext>2</mml:mtext></mml:msub><mml:mtext>O</mml:mtext></mml:mrow></mml:math> and [Cu(2dmepda)(bipy)(EtOH)]<mml:math id="E4" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>2</mml:mn><mml:mo>⋅</mml:mo><mml:mn>4</mml:mn><mml:mtext>EtOH</mml:mtext><mml:mrow><mml:mo>(</mml:mo><mml:mrow><mml:mtext>bipy=</mml:mtext><mml:mn>2</mml:mn><mml:mo>,</mml:mo><mml:msup><mml:mn>2</mml:mn><mml:mo>′</mml:mo></mml:msup></mml:mrow></mml:mrow></mml:mrow></mml:math>Bipyridine)

Devereux, Michael; McCann, Malachy; O'Shea, Denis; O'Connor, Mark; Kiely, Eileen; McKee, Vickie; Naughton, Declan; Fisher, Anna; Kellett, Andrew; Walsh, Maureen; Egan, Denise; Deegan, Carol

doi:https://doi.org/10.1155/BCA/2006/80283

Bioinorganic Chemistry and Applications

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Volume 2006 | Article ID 080283 | https://doi.org/10.1155/BCA/2006/80283

Synthesis, Superoxide Dismutase Mimetic and Anticancer Activities of Metal Complexes of 2,2-Dimethylpentanedioic Acid(2dmepdaH2) and 3,3-Dimethylpentanedioic acid(3dmepdaH2): X-Ray Crystal Structures of [Cu(3dmepda)(bipy)]2⋅6H2O and [Cu(2dmepda)(bipy)(EtOH)]2⋅4EtOH(bipy=2,2′Bipyridine)

Michael Devereux,¹Malachy McCann,²Denis O'Shea,¹Mark O'Connor,¹Eileen Kiely,¹Vickie McKee,³Declan Naughton,⁴Anna Fisher,⁴Andrew Kellett,^1,5Maureen Walsh,⁵Denise Egan,⁵and Carol Deegan⁵

Received10 Jan 2005

Revised23 Feb 2005

Accepted25 Feb 2005

Published16 Mar 2005

Abstract

2,2-dimethylpentanedioic acid (2dmepdaH2) and 3,3-dimethylpentanedioic acid (3dmepdaH2) reacted with copper(II) acetate to give [Cu(2dmepda)(H2O)3]2 (1) and [Cu(3dmepda)(H2O)3]2 (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H2O)]20.5phen (3), [Cu(2dmepda)(bipy)(H2O)]2 (4), [Cu(2dmepda)(bipy)(EtOH)]2⋅2EtOH (4A), [Cu(3dmepda)(phen)(H2O)]2 (5), and [Cu(3dmepda)(bipy)(H2O)]2⋅ (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]2 dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)–(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H2O)]20.5phen (3) was the most potent with activity that compares well to that of cisplatin.

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Copyright © 2006 Michael Devereux et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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